Neck swellings that appear on straining, crying, and Valsalva maneuver are usually suggestive of laryngocele. Phlebectasia of jugular veins can cause a similar sign but is rare compared to laryngocele. Jugular vein phlebectasia (JVP) is of unknown etiology and is caused by vein dilatation without tortuosity, which is rare in children. It transiently appears during straining as a soft cystic neck mass. Such cases are frequently misdiagnosed or managed inappropriately due to their rarity. We report a case of a four-year-old boy with right internal JVP and right hydrocele.